Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
  • C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
  • C09B62/4411—Azo dyes
  • C09B62/4413—Non-metallized monoazo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
  • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
  • C09B62/08—Azo dyes
  • C09B62/085—Monoazo dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
  • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
  • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
  • C09B62/507—Azo dyes
  • C09B62/51—Monoazo dyes

Definitions

• the invention is in the technical field of fiber-reactive azo dyes.
• the formula radical K means in particular a mono-, di- or trisulfonaphthyl radical, a monosulfophenyl, 2,4-disulfophenyl, 2,5-disulfophenyl, 3,5-disulfophenyl, a monochloromonosulfophenyl, a dichloro-monosulfo-phenyl, a monomethyl-monosulfo-phenyl, a monochloro-monomethyl-monosulfo-phenyl radical or a radical of the general formula (2f) in which R 3 , R 4 , Z and n have the meanings given above.
• the new azo compounds can be present both in acidic form and in the form of their salts. They are preferably in the form of the salts, in particular the alkali metal and alkaline earth metal salts, and are also preferably used in the form of these salts for dyeing (understood here and hereinafter in the general sense and including printing) of materials containing hydroxyl and / or carbonamide groups, in particular Fiber materials.
• the present invention further relates to processes for the preparation of the above-mentioned and defined azo compounds of the general formula (1). These processes are characterized in that a diazonium compound of an amine of the general formula (3) in which R 1 , R 2 , p, D and Y have the meanings given above, with a pyrazolone compound of the general formula (4) in which R and K have the meanings given above,
• the formula radical Y (which may be represented in K by the formula radical Z) can also be the ⁇ -hydroxyethyl Group mean.
• the compounds which can be prepared in accordance with the general formula (1), in which here Y or Z or both denote the ⁇ -hydroxyethyl group, can be converted into the corresponding compounds of the formula (1) according to the invention by means of a corresponding esterification or acylating agent, analogously to known procedures. transfer in which Y or Z stands for an ethyl group which is substituted in the ⁇ -position by an ester group.
• the preferred esterification here is sulfation, i.e.
• the amines of the general formula (3) which serve as starting compounds can be prepared analogously to known procedures, for example by reacting a diamino compound of the general formula H 2 ND-NH 2 with D of the abovementioned meaning with a dichlorotriazine compound of the general formula (6) given and defined above or by reaction of cyanuric chloride (2,4,6-trichloro-1,3,5-triazine) first with a diamino compound of the formula H 2 ND-NH 2 defined above to give a compound of the general formula (9) with D of the meaning given above and this can then be prepared with an amine of the general formula (8) given above and defined.
• dichlorotriazine compounds according to the general formula (6) can be prepared analogously to known procedures, for example by reacting cyanuric chloride with an amine of the general formula (8) given and defined above.
• the synthesis of the dichlorotriazine compound of the general formula (7) can be carried out, analogously to known procedures, by condensing cyanuric chloride with an aminoazo compound of the general formula (5) given and defined above or by reacting a diazonium compound of an amine of the general formula (9) given and defined above. with a pyrazolone compound of the general formula (4) defined above.
• Both the reaction of cyanuric chloride with an aminoazo compound of the general formula (5) for the compound of the general formula (7) and the reaction of cyanuric chloride with an amino compound of the general formula (8) to the compound of the general formula (6) can be carried out in organic or aqueous - organic medium. It is preferably carried out in an aqueous medium with the addition of acid-binding agents, such as alkali metal or alkaline earth metal ten, alkali or alkaline earth hydrogen carbonates or hydroxides or alkali acetates, the alkali and alkaline earth metals preferably being those of sodium, potassium and calcium; Acid-binding agents are also tertiary amines, such as pyridine or triethylamine or quinoline.
• acid-binding agents such as alkali metal or alkaline earth metal ten, alkali or alkaline earth hydrogen carbonates or hydroxides or alkali acetates, the alkali and alkaline earth metals preferably being those of
• condensation reactions are at a temperature between -10 ° C and +40 C, preferably between -10 o C and +30 C, most preferably at a temperature between 0 ° C and ⁇ 10 ° C and at a pH value between 1 , 0 and 7.0, preferably between 3.5 and 5, carried out.
• the inventive reaction of the dichlorotriazinylamino compounds of the general formulas (6), (7) and (9) with corresponding amino compounds of the general formula (5), the general formula (8) and the general formula H 2 ND-NH 2 defined above can also be carried out in an organic or aqueous-organic medium. However, they are preferably carried out in an aqueous medium, with an acid-binding agent, such as those given above, being added if necessary.
• the reaction of the amino groups with the chlorine of the triazine compounds in the processes according to the invention is preferably carried out at a temperature between 10 and 60 ° C., particularly preferably between 20 and 50 ° C., and at a pH between 2 and 9, in particular between 3 and 8 , carried out.
• the diazotization of the amino compounds of the general formula (3) or of the general formula (9) is carried out analogously to known procedures, for example in aqueous-organic and especially in an aqueous, acidic medium by nitrous acid.
• the reaction of the diazonium compounds with the pyrazolone compounds of the general formula (4) is also carried out analogously to known procedures, for example in aqueous-organic, but predominantly in an aqueous medium, in the slightly acidic to neutral, possibly very weakly alkaline pH range.
• Amino compounds of the general formula (8) with p equal to 1, which serve as starting compounds for the preparation of the compounds according to the invention, are, for example, 1-amino-3- (ß-sulfatoethylsulfonyl) benzene, 1-amino-2-methoxy-5- (ß -sulfatoethylsulfonyl) -benzene, 1-amino-2-methoxy-4- (ß-sulfatoethylsulfonyl) -benzene, 1-amino-2-methyl-5- ( ⁇ -sulfatoethylsulfonyl) -benzene, 1-amino-2-methyl- 4- (ß-sulfatoethylsulfonyl) benzene, 1-amino-4-methoxy-5- (ß-sulfatoethylsulfonyl) benzene, 1-amino-4-methyl-5- (ß-sulfatoeth
• Amino compounds of the general formula (8) with p equal to zero which can serve as starting compounds for the preparation of the compounds according to the invention, are, for example, aniline, 1-aminobenzene-3-sulfonic acid, 1-aminobenzene-3,5-disulfonic acid, 2-aminotoluene , 3-amino-toluene, 4-amino toluene, 2-amino-toluene-4-sulfonic acid, 2-amino-toluene-5-sulfonic acid, 2-amino-toluene-4,5-disulfonic acid, 2-amino-toluene-4,6-disulfonic acid, 3-amino toluene-6-sulfonic acid, 4-amino-toluene-2-sulfonic acid, 4-amino-toluene-3-sulfonic acid, 2-amino-anisole, 3-amino-anisole, 4-amin
• Pyrazolone compounds corresponding to the general formula (4) which serve as starting compounds for the preparation of the azo compounds according to the invention, are, for example, 1- (2'-sulfophenyl) -3-methyl-pyrazol-5-one, 1- (3'-sulfophenyl) -3 -methyl-pyrazol-5-one, 1- (4'-sulfophenyl) -3-methyl-pyrazol-5-one, 1- (2 ', 4'-disulfophenyl) -3-methyl-pyrazol-5-one, 1- (3 ', 5'-disulfophenyl) -3-methyl-pyrazol-5-one, 1- (2', 5'-disulfophenyl) -3-methyl-pyrazol-5-one, 1- (2', 5'-disulfophenyl) -3-methyl-pyrazol-5-one, 1- (2'- Chloro-4'-sulfophenyl) -3-methyl-pyrazol-5-one,
• diamino compounds corresponding to the general formula H 2 ND-NH 2 given above which can serve as starting compounds for the preparation of the azo compounds according to the invention, are 1,3-diaminobenzene-4,6-disulfonic acid and 1,4-diaminobenzene-2,5-disulfonic acid.
• the compounds of general formula (1) prepared according to the invention can be separated and isolated from the synthesis solutions by generally known methods, for example either by precipitation from the reaction medium by means of electrolytes, such as sodium chloride or potassium chloride, or by evaporation of the reaction solution, for example spray drying.
• a buffer substance can be added to this reaction solution.
• the compounds of the general formula (1) according to the invention have fiber-reactive properties and very good dye properties. They can therefore be used for dyeing (including printing) materials containing hydroxy groups and / or carbonamide groups.
• the solutions obtained in the synthesis of the compounds according to the invention if appropriate after adding a buffer substance, if appropriate also after concentration, can be used directly as a liquid preparation for dyeing.
• the present invention therefore also relates to the use of the compounds of the general formula (1) according to the invention for dyeing (including printing) materials containing hydroxyl and / or carbonamide groups and processes for their use on these substrates.
• the materials are preferably used in the form of fiber materials, in particular in the form of textile fibers, such as yarns, packages and fabrics. This can be carried out analogously to known procedures, by applying the monoazo compound of the general formula (1) in dissolved form to the substrate or introducing it into it and on it or in it, optionally by exposure to heat and / or optionally by the action of an alkaline agent , fixed.
• Materials containing hydroxyl groups are of natural or synthetic origin, such as cellulose fiber materials or their regenerated products and polyvinyl alcohols.
• Cellulose fiber materials are preferably cotton, but also other vegetable fibers, such as linen, hemp, jute and ramie fibers; Regenerated cellulose fibers are, for example, cellulose and viscose rayon.
• Materials containing carbonamide groups are, for example, synthetic and natural polyamides and polyurethanes, in particular in the form of fibers, for example wool and other animal hair, silk, leather, polyamide-6,6, polyamide-6, polyamide-11 and polyamide-4.
• the compounds of the general formula (1) according to the invention can be applied and fixed on the substrates mentioned, in particular on the fiber materials mentioned, by the application techniques known for water-soluble, in particular for the water-soluble fiber-reactive dyes. Such staining and fixing methods are described in the literature in large numbers.
• Dyeing is preferably carried out in an aqueous bath at temperatures between 60 and 105 ° C., if appropriate at temperatures up to 120 ° C. under pressure and, if appropriate, in the presence of conventional dyeing auxiliaries.
• the procedure can be such that the material is introduced into the warm bath and this is gradually heated to the desired dyeing temperature and the dyeing process is completed at this temperature.
• the neutral salts accelerating the removal of the dye can also be added to the bath only after the actual dyeing temperature has been reached.
• cellulose fibers which are single-phase, for example in the presence of sodium bicarbonate or another acid-binding agent in the printing paste and by subsequent steaming at 100 to 103 ° C, or two-phase, for example by printing with neutral or weakly acidic printing ink and subsequent fixing either by passing through a hot electrolyte-containing alkaline bath or by padding with an alkaline electrolyte-containing pad liquor and then lingering this treated material or vapors or treatment with dry heat, you can obtain strong-colored prints with good shape of the contours and a clear white background. The failure of the prints is only slightly dependent on changing fixing conditions.
• Hot air from 120 to 200 ° C is used for fixing with dry heat using the usual heat-setting processes.
• superheated steam and pressure steam at temperatures up to 160 ° C can also be used.
• the acid-binding agents and the fixation of the compound of formula (1) on the cellulose fibers are, for example, water-soluble basic salts of the alkali metals and also alkaline earth metals of inorganic or organic acids or compounds which release alkali in the heat.
• the alkali metal hydroxides and alkali metal salts of weak to moderately strong inorganic or organic acids should be mentioned, where of the alkali compounds, preferably the sodium and potassium compounds are meant.
• Such acid-binding agents are, for example, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium formate, sodium dihydrogen phosphate, disodium hydrogen phosphate, sodium trichloroacetate, water glass or trisodium phosphate.
• the compounds (dyes) according to the invention are chemically bound to the cellulose fiber: in particular the cellulose dyeings show excellent wet fastness properties after the usual aftertreatment by rinsing to remove unfixed dye components, especially since they are not Fixate dye portions easily washed out because of their good cold water solubility.
• the dyeings on polyurethane fibers or natural or synthetic polyamide fibers are usually carried out from an acidic environment.
• acetic acid and / or ammonium sulfate and / or acetic acid and ammonium acetate or sodium acetate can be added to the dyebath in order to obtain the desired pH.
• conventional leveling aids such as, for example, based on a reaction product of cyanuric chloride with 3 times the molar amount of an aminobenzenesulfonic acid and / or an aminonaphthalenesulfonic acid and / or on the basis of a reaction product of, for example, stearylamine with ethylene oxide.
• the material to be dyed is introduced into the bath at a temperature of approx. 40 ° C, agitated there for some time, the dyebath is then adjusted to the desired weakly acidic, preferably weakly acetic acid, pH value and the actual dyeing at one Temperature between 60 and 98 ° C carried out.
• the colors can also be carried out at boiling temperature or at temperatures up to 120 ° C (under pressure).
• the dyeings and prints produced with the compounds of the general formula (1) according to the invention are generally distinguished by clear, greenish yellow, reddish yellow to yellowish orange shades and high color strengths.
• the dyeings and prints on cellulose fiber materials have very good light fastness and good to very good wet fastness properties, such as wash, walk, water, sea water, over-dyeing and perspiration fastnesses, furthermore good pleating fastness, ironing fastness and rubbing fastness.
• the use of the compounds of the general formula (1) according to the invention is also of importance for the fiber-reactive dyeing of wool.
• wool which has been given a felt-free or low-felt finish (cf., for example, H.Rath, Textbook of Textile Chemistry, Springer-Verlag, 3rd edition (1972), pp. 295-299, in particular the finishing according to the so-called Hercosett process (p . 298); J. Soc. Dyers and Colourists 1972, 93 - 99, and 1975, 33 - 44) dye with very good fastness properties.
• the process of dyeing on wool is carried out in the customary and known manner of dyeing, in that the fiber-reactive compound of the general formula (1) is preferably first subjected to the exhaust process from an acid dyebath with a pH of about 3.5 to 5.5 while checking the pH and towards the end of the dyeing time the pH value is shifted to a neutral and possibly weakly alkaline range up to a pH value of 8.5, in order to achieve the full reactive bond between this dye of the formula (in particular if high color depths are desired) 1) and bring about the fiber. At the same time, the non-reactive dye component is removed.
• the procedure described here also applies to the production of dyeings on fiber materials from other natural polyamides or from synthetic polyamides and polyurethanes.
• the dyeings are carried out at temperatures from 60 to 100 ° C, but they can also be carried out in closed dyeing machines at temperatures up to 106 ° C. Since the water solubility of the compounds of the general formula (1) is very good, they can also be used advantageously in conventional continuous dyeing processes.
• the color strength of the compounds of the general formula (1) according to the invention is very high. They provide clear, greenish yellow and reddish yellow to yellowish orange dyeings on the fiber materials, especially when reactive dyeing wool. When using dyeing temperatures of 100 to 106 ° C a high bath exhaustion can be determined.
• an otherwise customary ammoniacal aftertreatment of the dyed goods can be dispensed with.
• they surprisingly show a very good color build-up, the brilliant nuance being retained even in deep tones.
• they show good combinability with other fiber-reactive wool dyes, which enable surprisingly level dyeing of the fiber.
• material made of wool fibers of different provenance can be dyed with the compounds according to the invention.
• a customary leveling aid such as, for example, N-methyl taurine, can optionally be added.
• the compounds according to the invention also give level dyeings on wool which has been made free or low in felt. With light to medium color depths is also without ammoniacal after treatment to achieve a very good level of wetness, although an ammoniacal aftertreatment may be preferred.
• the excellent alkaline perspiration fastness and very good wash fastness at 60 ° C are particularly good wet fastness properties.
• Parts by weight relate to parts by volume such as kilograms to liters.
• the compounds described by formula in the examples are given in the form of the free acids; in general, they are prepared and isolated in the form of their salts, in particular sodium or potassium salts, and used in the form of their salts for dyeing.
• the starting compounds mentioned in the following examples, in particular table examples, in the form of the free acid as such or in the form of their salts, preferably alkali metal salts, such as sodium or potassium salts, can be used in the synthesis.
• the monoazo compound according to the invention thus produced is isolated in a conventional manner, for example by evaporation or spray drying of the neutral synthesis solution or by Salt out with an electrolyte salt, such as potassium chloride.
• An electrolyte-containing yellow powder is obtained, which is the alkali metal salt, such as potassium salt, of the compound of the formula contains.
• This azo compound according to the invention shows very good dye properties, in particular very good fiber-reactive dye properties, and delivers on the materials mentioned in the description, such as in particular cellulose fiber materials, such as cotton, according to the application and fixing methods customary in the art, in particular those described for fiber-reactive dyes and applied, strong, clear greenish yellow dyeings and prints of good light fastness and good wet fastness, such as, in particular, good fastness to washing, milling, sweating and overdyeing.
• the monoazo compound according to the invention produced here according to this process variant is isolated in a conventional manner, for example according to the information in Example 1; it is identical to the monoazo compound according to the invention produced according to Example 1 and accordingly has the same good coloring properties and good fastness properties as the compound according to the invention which is produced according to Example 1.
• Example 1a To prepare a monoazo compound according to the invention, the procedure of Example 1 is followed, except that in Example 1a) the 4- ( ⁇ -sulfatoethylsulfonyl) aniline is replaced by 156 parts of 4- ( ⁇ -thiosulfatoethylsulfonyl) aniline.
• an electrolyte-containing powder which contains the alkali metal salt, such as sodium and / or potassium salt, of the compound of the formula contains.
• This compound according to the invention shows very good dye properties and, for example, provides strong, greenish yellow dyeings and prints of good lightfastness and wet fastness properties, such as good fastness in laundry, on cotton by the application and fixing methods customary in the art for fiber-reactive dyes.
• Example 2 To prepare a monoazo compound according to the invention, the procedure of Example 2 is followed, except that the aqueous solution of 4- ( ⁇ -sulfatoethylsulfonyl) aniline used in Example 2b) is replaced by a solution of 39 parts of 4-vinylsulfonyl-aniline in 200 parts by volume of acetone .
• an electrolyte-containing powder which contains the alkali metal salt, such as, for example, the sodium salt of the compound of the formula contains.
• This compound according to the invention also shows very good dye properties and, according to the application and fixing methods customary in the art for fiber-reactive dyes, for example on cotton, gives strong, greenish yellow dyeings and prints of good light and wet fastness properties.
• Example 2b To prepare a monoazo compound according to the invention, the procedure of Example 2 is followed, except that in Example 2b) the aqueous solution of 4- ( ⁇ -sulfatoethylsulfonyl) aniline is replaced by 46 parts of powdered 4- ( ⁇ -chloroethylsulfonyl) aniline.
• This monoazo compound according to the invention has very good dye properties; one obtains with it, for example, on cotton using the application and fixing method customary in the technology for fiber-reactive dyes the strong, greenish-yellow colorations with good light and wet fastness properties.
• the monoazo compound according to the invention thus produced is isolated in a conventional manner, for example by precipitation from the reaction solution using potassium chloride. After suction and drying and grinding of the precipitate, a yellow, electrolyte-containing powder is obtained, which contains the alkali metal salt, such as potassium salt, of the monoazo compound according to the invention, which is given by formula in Example 1.
• the monoazo compound according to the invention produced according to the process variant described here and identical to that of Example 1 shows the same good dyeing see properties and authenticity of the strong, clear, greenish yellow dyeings and prints available with it.
• the procedure for producing a monoazo compound according to the invention is carried out in accordance with the procedures of Example 1, but the 1,3-diaminobenzene-4,6-disulfonic acid used in Example 1a) is replaced by the same amount of 1,4-diaminobenzene-2,5-disulfonic acid.
• the corresponding alkali metal salt of the compound of the formula is obtained which also has very good dye properties.
• Example 2 The procedure for producing a monoazo compound according to the invention is as in Example 2, but 130 parts of the isomeric aminoazo compound of the formula are used instead of the azo starting compound used in Example 2a) into the acylation reaction, the monoazo compound according to the invention of Example 7 above is obtained with the same good dyeing properties and good fastness properties.
• the pressure thus produced is then completed by rinsing with cold and hot water, by washing with a neutral detergent and rinsing again with water. After drying the goods, a strong greenish yellow print with very good light fastness and very good wet fastness properties is obtained.
• a fabric made of mercerized cotton is padded with an aqueous dye liquor at 20 ° C. with a liquor absorption of 80%, based on the weight of the goods, in liters of 20 g of the sodium salt of the azo compound according to the invention from Example 1, 2 or 6 and 18 g of 33% contains sodium hydroxide solution.
• the padded fabric is wrapped on a dock, wrapped in foil and left at room temperature for eight hours. It is then finished by rinsing with cold water, by treating with an aqueous bath containing a little acetic acid and by rinsing again in cold and hot water. After drying, a deep greenish yellow color with very good light fastness and very good wet fastness is obtained.
• 100 parts of a fabric made of mercerized cotton are treated for 10 minutes at 60 ° C. in 3000 parts by volume of an aqueous dyebath which contains 5 parts of the sodium salt of the compound according to the invention from Example 1 and 150 parts of anhydrous sodium salt. After this 10 minute treatment, 15 parts of anhydrous sodium carbonate and 4 parts of 33% sodium hydroxide solution are added. The dyeing is continued at 60 0 C for 60 minutes. The dyed fabric is then finished in the customary manner, for example in Application Example 2. A strong, greenish yellow color is obtained which has very good light fastness and very good wet fastness properties.
• a woolen fabric 100 parts are introduced into a 40 ° C. warm dyebath which consists of 3000 parts of water, 2 parts of the sodium salt of the compound according to the invention described in Example 1, 0.15 part of an adduct of 12 moles of ethylene oxide and 1 mole of stearylamine, 2 parts of ammonium acetate and 2 parts of 60% aqueous acetic acid.
• the dyeing temperature is raised to the boiling temperature within 30 minutes and the dyeing is then continued at 100 ° C. for 60 minutes. After the usual washing and finishing of the wool dyeing obtained, this wool fabric shows a strong, greenish-yellow hue of very good lightfastness and very good wetfastness.
• the other monoazo compounds according to the invention described here in the exemplary embodiments and table examples can also be used in the dyeing and printing processes.
• very strong dyeings and prints of good light and wet fastness properties are also obtained in the shades that are appropriate for the particular embodiment or Table example are given.

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• 1981
  • 1981-08-19 DE DE19813132724 patent/DE3132724A1/de not_active Withdrawn
• 1982
  • 1982-08-12 IN IN948/CAL/82A patent/IN157428B/en unknown
  • 1982-08-14 DE DE8282107401T patent/DE3262676D1/de not_active Expired
  • 1982-08-14 EP EP82107401A patent/EP0072557B1/fr not_active Expired
  • 1982-08-17 KR KR8203680A patent/KR890002348B1/ko active
  • 1982-08-18 JP JP57142238A patent/JPS5849752A/ja active Pending
  • 1982-08-19 CS CS826083A patent/CS232734B2/cs unknown
  • 1982-08-19 BR BR8204869A patent/BR8204869A/pt unknown
• 1985
  • 1985-10-14 IN IN728/CAL/85A patent/IN162616B/en unknown

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